Sodium Hydroxide → HCID 67109924, compound

HRID 455320Notes

Reaction equation

HRID 455320 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:48]([O:50]C)=[O:49])=[N:11][C:12]([N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:47])[CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[CH2:38][NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:21][CH2:20]2)=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO.O>[CH2:1]([O:8][C:9]1[C:10]([C:48]([OH:50])=[O:49])=[N:11][C:12]([N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:47])[CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[CH2:38][NH:39][C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[CH2:21][CH2:20]2)=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67110480HCID 67110480, compound

Product 1

HCID 67109924HCID 67109924, compoundYield 52.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 8-(benzyloxy)-5-(4-(5-(2-((tert-butoxycarbonylamino)methyl)-5-fluorophenoxy)pentanoyl)piperazin-1-yl)-1,6-naphthyridine-7-carboxylate (Example 5.1; 1.1 mmol) was dissolved in a mixture of THF (6 ml), methanol (6 ml) and water (6 ml). Sodium hydroxide (7.5 mmol) was added and stirred for 2 days. The organic solvent was removed under vacuum, and the residue washed with diethyl ether. The aqueous residue was acidified with 1 N HCl to pH=8-9. The mixture was washed with ethyl acetate. The aqueous phase was acidified with 1N HCl to pH 3-4. The mixture was extracted with ethyl acetate and the organic layer was washed with brine and dried over Na2SO4. The solvent was removed under vacuum to afford the title compound (0.4 gr) that was used as such in the next step.

Workup

  1. customThe organic solvent was removed under vacuum
  2. washthe residue washed with diethyl ether
  3. washThe mixture was washed with ethyl acetate
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-060c2e64ae254b31b34e799dc40c38b5
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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